


Up ‘N Comers

by cyncitymojo



Category: Supernatural, Supernatural RPF
Genre: Aliases, Alternate Universe - Vegas, Amateur Night!Jared, Bartender!Jensen, First Time Wincest Implied, Flair bartending, Hurt Sam Winchester, M/M, Masturbation on camera, Mugging, My AU & Trope Bingo Masterlist, Other, Roleplay Suggested, SPN AU & Trope Bingo
Language: English
Status: Completed
Published: 2018-01-30
Updated: 2018-01-30
Packaged: 2019-03-10 07:21:35
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,796
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/13497372
Author URL: https://archiveofourown.org/users/cyncitymojo/pseuds/cyncitymojo
Summary: Sam and Dean Winchester have an annual trip to Vegas that lasts for a week to ten days, mainly at Dean's insistence. There is always an 'adventure,' even if it's not related to the supernatural. This year is not different, chaos still ensues and plans still go awry…





	Up ‘N Comers

**Author's Note:**

> Square filled: BARTENDER!JENSEN
> 
> ***I really hope this fills the designated square! It was fun to imagine and put on paper, but if not I'll chock it up to beginner's learning curve. :)
> 
> Thank you [jessie_cristo](https://archiveofourown.org/users/jessie_cristo/pseuds/jessie_cristo) for prompting me and letting me run with it!
> 
> Written/created for [SPN AU Bingo](https://spnaubingo.tumblr.com/) Challenge on Tumblr
> 
> Thank you lovelies, my beta [Missyswife37](https://archiveofourown.org/users/Missyswife37/pseuds/Missyswife37) and Mod Anna for everything!

*****

 

Upon arrival in their Las Vegas motel room, Dean, as usual, left Sam most of their fraudulent credit cards and was off on his own. He had taken most of the cash. It turned out he was an infamous flair bartender with the alias Jensen "Flashtender" Ackles. He had quite the local following. 

The elder hunter secretly competed in Legends of Bartending, a competition that had awarded them with most of their money each year. He used the cash he had taken for the entry fee. Over the years, unbeknown to Sam, “Jensen” repeatedly won the championship and the pot of cash by the fifth day of their vacation. They now rarely found themselves in a jam where they needed to hustle or use the defrauded credit cards. 

Sam, assuming his brother is merely drinking and screwing his way through Vegas, wanders around trying to get out of the funk of being alone. Somewhere toward the end of Fremont Street, Sam emerges from his daydreaming and figures out he is in an alley and his surroundings look sketchy. While silently admonishing himself for not paying better attention to his surroundings, he runs into 3 guys and gets mugged. 

They picked the wrong guy, of course, and got molly-whopped. However, they managed to snag the wallet that held the credit cards. Sam was too stubborn to call Dean for help and thought he'd never hear the end of it anyway. Applying for more cards would have taken too long, so he resigned to having no other choice than to take a leaf out of Dean's book and hustle pool. He had five hundred in cash hidden in his boot for emergencies. This was nothing, if not an emergency. 

In Vegas though, con artists and pool hustlers are a dime a dozen, and these were not the amateurs that the young hunter was accustomed to. These scam artists ended up MUCH better than Sam. He swiftly lost the last of the cash he carried. To top it off he found himself in a deficit of five hundred more to the last guy he played against. He did not know what he was going to do. 

The guy was pretty sleazy, and had been checking Sam out the whole time. He offered Sam a way to pay off his debt in an alternative way. Sam was taken aback. He was NOT about to do anything with this sleazeball just to pay up. Sam tensed up, ready for one hell of a fight. The guy laughed and told him not to be so full of himself. 

“One video, one little private film of you doing something you’d really enjoy, solo. Stallion like you’d clear two grand, easy. Sounds like a win-win to me kid. I’ll be taking my cut of course. Just bring it over to my place, Up ‘N Comers, tomorrow night.” 

Sam figured one video would equal him not having to crawl back to Dean like a whipped dog, he could pay what he owed and would still have extra to try to enjoy Vegas himself for the rest of their week off. 

He goes along with it. 

*** 

Three Days Later: 

There were several flat screens in the Up ‘N Comers bar showing a variety of things for entertainment, but there was one huge flat screen near the end of the bar. The screen was flipping from one ridiculous preview scene to the next. The amateurs were looking directly into the camera, but not looking very convincing. Each one was a perfect example of what someone looks like when they’re trying too hard, phoning it in, or just plain uncomfortable. 

Jensen “Flashtender" Ackles was grateful for the cringe-worthy material because it meant less distraction for him during the semi-finals. Once he was done qualifying for the finals and taking out one of the brother-sister team who had joined him in this stage of the Flair competition for the last few years, he'd be able to accompany them both back to their hotel suite, as was their annual tradition. 

It was their fourth day of vacation and Jensen was really in the groove. He was also missing someone special. He was not used to being away from his brother so long unless something was wrong, even though they did this every year. It was why he swept out of the room so fast; rip the band-aid off so to speak. 

By day five the competition would be over, and he could stop being Jensen “Flashtender” Ackles for another year. The last few days would be for grilling his baby brother and giving him a hard time about how he spent his alone time. He assumed the lovable nerd would have found some obscure tours or a museum to get lost in. 

Now, he was doing the most impressive balance and twirling patterns with perfect form, speed, and accuracy. By the time he had finished his set and was humbly accepting the applause from the happy patrons who had his signature cocktails in hand, he looked up just in time to catch the first full scene on the big screen. He found himself frozen in place, captivated. 

The featured amateur of the evening was spellbinding. The camera was aimed from a low position, head-on. Long, tan legs bent at the knees and spread wide, framed huge hands sliding down smooth, muscled thighs. They met at the junction between, which was an apparently well-prepped, glistening opening topped with heavy, firm balls and a rod the size of a tree trunk. One hand swept up to caress sweaty, marble-like abs and tweak a flushed, perked nipple. 

Jensen was instantly weak in the knees and went to perch on a barstool. He couldn’t believe this was an amateur. He had to discreetly palm himself to relieve his rapid erection. He looked at the corner of the screen to see the name that had been posted, it said Jared. ‘Nice alias, way to keep it simple, hot stuff,’ he thought. He re-focused on the action. 

The other hand was busy squeezing and tugging testicles as if it was staving off an explosion. Then, it went for the rock hard, twitching shaft and started a steady stroke. Jensen looked up again at the broad chest and saw brown, floppy hair hiding a familiar profile. He did a double take when he the left knee moved just right, and he could clearly make out SAM’s anti-possession tattoo! 

Jensen was out of his mind, nearly falling from the stool. Instead of instantly deflating and getting the hell out of there, he nearly shot his load. That was his brother on screen looking like solo porn was his second career and all Jensen could do was sit there and shiver with how turned on he was. Sam definitely had some explaining to do. 

How? Why? And when the hell did Sammy start packing heat like that? 

“Dean, please…” 

Jensen barely heard the murmur above the commotion in the bar, but he heard it. At the same time, he watched Sam penetrate himself with three fingers. They disappeared inside him so easily, Jensen was gasping for air. He forced his legs to move, and he vanished from the bar completely forgetting the twins. 

***

‘Jensen,’ no, _Dean_ practically ripped the door off the hinges when he got to their room. Sam was standing in the doorway of the bathroom, holding a rather sizeable knife, in a towel. He apparently was fresh out the shower, and on high alert. When Sam realized it was his older brother, he put the knife down and set his bitchface in motion. 

Dean froze, not sure he could broach the subject this instant, with his brother half-naked, much less at all. Then he remembered the scene at the bar and looked everywhere but at Sam. He was flushed and flustered that all he could think of was ‘Jared' and the short amount of time he brought Dean nearly to public indecency. 

"Look, Sammy, I uh, I need to ask you something. I need you to be str- um, honest with me. Alright? Can you do that?” 

“Of course, Dean. I kinda have a question for you too.” 

Dean directly faced his brother then. He noticed the light bruising on his face and at his ribs. “WHAT THE HELL?!” He made it to Sam in two strides and began to check for any further injuries, all else forgotten except… 

“Sammy… are you ‘Jared’?” 

“… Shit. I knew it. I thought I saw you at that bar that night. I didn’t want to believe that I left that video anywhere you might see it, but I knew. No one looks-,” he began and then tensed, feeling a shift in the air. He’d watched his mysterious bartender’s back from a distance and later gone to the room and came, ‘Jensen’ on his lips. “Yes, I am. Are you Jensen? Is that why we come here every year?” 

“OK, that explains my baby brother spread-eagle on a screen for the world to see, but why?" he asked, irritation and tension building. “Does this have anything to do with you looking like you got into a scrap match on the playground after school? Did someone force you to do this Sammy?” 

“Dean, calm down ok, it is a long story. For the record, no one forced me. I will tell you after you answer me. Please, I am embarrassed enough already.” He hit his older brother with the deepest puppy eyes in his arsenal. 

“Fine, yeah, I am Jensen. I do this Bartending competition thing that keeps us in some extra, honest, cash. I do that for you Baby, I know how much you hate all things shady and underhanded.” He was gradually coming down from his anger-kill endorphins and did not realize what he said. Sam, however, caught the slip. 

“Um, Baby? OK, ‘Flashtender,’ what’s up? You see something you like?” Sam forgot that he was in nothing more than a small-to-him hotel towel. 

Dean felt the blush of ‘oops,’ then heard the challenge in a voice he recognized as ‘Jared’s,’ and looked into darkened, stormy eyes. He switched to his cocky persona Jensen and said, “Hey _Jared_ , chicks AND dicks flock to the Flashtender.” He placed his hands on ‘Jared’s’ hips, remembering how close they were after Dean had panicked. 

‘Jensen’ grinned at ‘Jared’ and tugged slightly at the fold at the top of the towel and watched it flutter to the floor. He thought the camera added weight, but clearly ‘Jared’ and the weapon he was packing was no illusion. He licked his lips and felt the younger mystery’s gaze on him as well. 

“Show me what you did with that thing on screen. I missed the ending.”

*****

**Author's Note:**

> There was an actual Legends of Bartending, World Bartender Championship competition that would test the bartender on four disciplines of bartending: accuracy, speed, working flair, and exhibition flair. It was in Las Vegas annually for at least 12 years until 2010. It has since been discontinued. This was such an inspiration though and since everything surrounding it is fiction, it was nice to have something to reference.


End file.
